1-(3-bromophenyl)-2,2,4,4,4-pentafluoro-3,3-dihydroxybutan-1-one | 1616792-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-bromophenyl)-2,2,4,4,4-pentafluoro-3,3-dihydroxybutan-1-one
• CAS: 1616792-38-1
• 化学式: C₁₀H₆BrF₅O₃
• 分子量: 349.052
• InChiKey: GBTQBMDPERDWHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-苯基-1,2,3,4-四氢异喹啉 、 1-(3-bromophenyl)-2,2,4,4,4-pentafluoro-3,3-dihydroxybutan-1-one 在 四氯化碳 、 tris(2,2'-bipyridyl)ruthenium dichloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以52%的产率得到2,2-difluoro-1-(3-bromophenyl)-2-(2-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone
  参考文献：
  名称：

  Visible-light-induced direct C(sp3)–H difluromethylation of tetrahydroisoquinolines with the in situ generated difluoroenolates

  摘要：

  公开了一种可见光促进的四氢异喹啉C(sp3)-H二氟甲基化反应，该反应使用稳定且易于制备的α，α-二氟基gem-二醇作为CF2源。

  DOI：

  10.1039/c4cc02768j

文献信息

• Synthesis of α,α-difluoro-β-amino carbonyl-containing sulfonamides and related compounds
  作者：Chen Xie、Lingmin Wu、Jie Zhou、Haibo Mei、Vadim A. Soloshonok、Jianlin Han、Yi Pan

  DOI：10.1016/j.jfluchem.2015.01.004

  日期：2015.4

  Mannich addition reactions between in situ generated α,α-difluoroenolates and various N-sulfonyl imines readily occur with exceptionally high reaction rates at ambient temperature. The method features remarkable generality and enjoys operationally convenient conditions underscoring its practicality and methodological importance for preparation of sulfonamides bearing β-amino-α,α-difluoro ketone moiety

  在环境温度下，原位生成的α，α-二氟烯酸酯与各种N-磺酰基亚胺之间的曼尼希加成反应很容易发生。该方法具有显着的通用性，并具有操作方便的条件，这突出了其制备具有β-氨基-α，α-二氟酮部分的磺酰胺的实用性和方法学重要性。
• Generalized access to fluorinated β-keto amino compounds through asymmetric additions of α,α-difluoroenolates to CF₃-sulfinylimine
  作者：Chen Xie、Lingmin Wu、Haibo Mei、Vadim A. Soloshonok、Jianlin Han、Yi Pan

  DOI：10.1039/c4ob01575d

  日期：——

  CF3-containing chiral imines readily react with α,α-difluoroenolates affording a novel type of β-keto-amino compounds featuring the R-CO-CF2-CH(NH2)-CF3 moiety. The reactions feature exceptional generality allowing preparation of various aromatic, hetero-aromatic and aliphatic derivatives in high yields and diastereoselectivity. The products are configurationally stable and can be transformed to more

  含CF 3的手性亚胺容易与α，α-二氟烯酸酯反应，得到新型的具有R-CO-CF 2 -CH（NH 2）-CF 3部分的β-酮-氨基化合物。该反应具有出色的通用性，可以高产率和非对映选择性地制备各种芳族，杂芳族和脂族衍生物。产品在结构上是稳定的，可以转化为官能度更高的复杂化合物。
• Divergent Reaction of Activated Pyridines with α,α-Difluorinated <i>gem</i>-Diols: Regioselective Synthesis of <i>gem</i>-Difluorinated Dihydropyridines and Dihydropyridones
  作者：Koushik Patra、Mallu Kesava Reddy、Sumitava Mallik、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.2c01445

  日期：2022.6.10

  The nucleophilic reactivity of α,α-difluorinated gem-diols toward activated pyridinium salts has been capitalized in a highly regioselective fashion, offering biologically relevant 1,4-dihydropyridines and 3,4-dihydro-2-pyridones adorned with the valuable gem-difluoromethylene motif. The protocol is scalable as well as high yielding and accommodates a broad range of substrates and functional groups

  α,α-二氟化偕二醇对活化的吡啶鎓盐的亲核反应性已以高度区域选择性的方式被资本化，提供了生物学相关的 1,4-二氢吡啶和 3,4-二氢-2-吡啶酮，并装饰有有价值的偕二氟亚甲基主题。该协议具有可扩展性和高产率，并适用于广泛的底物和功能组。此外，通过产品多样化展示了二氟化氧杂氮杂双环[3.3.1]壬烷骨架的合成。
• Divergent Reactivity of <i>gem</i>-Difluoro-enolates toward Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of α-Ketoamides
  作者：Mallu Kesava Reddy、Isai Ramakrishna、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.8b01900

  日期：2018.8.3

  An amination reaction of in situ generated gem-difluoro-enolates has been explored with electrophilic nitrogen sources. While their exposure to azodicarboxylates smoothly produced fluorinated alpha-amino ketones, reaction with nitro-soarenes (nitroso aldol reaction) furnished alpha-ketoamides in very high yields (up to 94%). The reaction is very fast (typically completed within 5 min) and scalable and tolerates various sensitive functional groups. Synthetic utility of this process was highlighted through the production of diverse nitrogen heterocycles and an orexin receptor antagonist.